I went semi-viral on Twitter recently, so there are a lot of new subscribers this week. For those of you who are new, in these newsletters I usually publish excerpts and personal takeaways from the best readings, conversations, and realizations I’ve experienced recently.

This week is a bit different: I am attempting to answer the question, “How do I become a killer?”

For context, I’m a VC who studied CS & English at Harvard and dropped out for a few semesters to work for startups backed by General Catalyst, Emmett Shear, Foundry Group, and various professional athletes.

Question

Goal: Become a killer

My job gives me an unbelievable proximity to greatness.

I get to meet, talk to, and ideate with dozens of people whom books should be written about: self-made billionaires, current and former executives of Fortune 50 companies, and people in my age group who will directly change the world more than I ever will.

As my age 25 year comes to close, I’ve been thinking a lot about becoming a killer. As I tweeted last year, there’s a subtle difference between being a grinder and being a killer. Being in rooms with killers means very little if I can’t become a killer myself. And, to be honest, I’ve really struggled to come up with a plan.

A career is a journey from being paid for promise to being paid for pedigree. For professionals both young and old, there’s a few “put up or shut up” points in the middle that make or break their careers. My next one is coming soon.

As a 25-year-old investor, as best I can tell, your primary value is getting shit done in a timely fashion. These are mostly menial tasks to start, though I’ve been surprised how much executing seemingly-menial tasks engenders trust from competent people.

I think this is because you are progressively seeing more and more of the same inputs, and by effectuating the will of an entrepreneur, you as an investor are demonstrating the ability to convert common inputs into the entrepreneur’s vision, which is the purpose of all startups.

All investment jobs are service jobs. I think early-stage private investors, at their best, primarily service the companies in their portfolio. (I am biased and fortunate in this regard: Since we are a single-LP fund and our LP is very smart, we spend comparatively less time schmoozing fund investors than most other VCs.) So, in my pursuit of killer edge, I am really trying to best: 1) find compelling founders, and 2) effectuate their vision.

Path forward: Become “that guy”

One way I characterize competence is being known as “The X Guy.” For example, I’m known by a lot of friends as “The Sports Card Guy.” Once upon a time, I flew across the country to attend sports collectible trade shows and flipped over $100k of inventory for a few years in a row. Once upon another time, I was CEO of a sports card-related company backed by several NBA and MLB players you’ve likely heard of.¹

My absolute worst nightmare would be walking into a room in five years, only for a friend to tell a stranger, That’s Sam, he’s the Investor Guy. In other words, “That’s Sam, his primary value is as a gatekeeper to capital.”

A good way to speedrun becoming a killer investor is to have unfair advantages. However, this mostly means your “X Factor” is from before you were an investor. “He’s the guy that helped build Uber,” or, “She’s the gal who found Pied Piper for Kleiner.” To me, a 25-year-old investor, this is immensely unsatisfying, as it suggests success in the craft of investing is a lagging indicator of competence. Since I am currently an investor, I’m most concerned with how to become a killer in the confines of an investment firm.

Observation: Most VC career advice is BS

Common advice to young venture capitalists is to “get points on the board.” In other words, “Spray and pray within the system you work, and have as many investments attributed to you as possible. It only takes one success to build a career.” While this advice is practical, it’s also bullshit when it comes to becoming a killer.

In writing, it’s very hard to be profound without trying to be profound. In investing, it’s likewise very hard to find a generational company without trying to find a generational company. Thus, spraying and praying is antithetical to becoming a killer, if you care about process and repeatability.

Curious to me is the ability for firms to manufacture someone’s lore. “She’s the youngest partner in firm history,” or “He was the analyst on the Facemash deal,” or “He’s Forbes 30u30” go a long way in establishing reputation. But what do those anecdotes actually say about someone’s competence? “Some rich people deemed this person worthy of being in the room before they are equally rich.” Okay? Seems like another, fancier way of saying, “This person is a gatekeeper to capital.”

It is, however, impossible to ignore the “self-fulfilling prophecy” motion of some of today’s best private investors. Sarah Guo of Conviction was the youngest partner in Greylock history. Pat Grady of Sequoia was once the youngest person Sequoia ever hired, and he now co-runs the place. (Coincidentally, Sarah and Pat are married. I’ve never met either, but I think they are both two of the smartest folks in early-stage investing today.)

The new “lifelong investor” archetype suggests that there is a viable path to greatness for someone like me in this industry. I am trying to determine, however, if it exclusively related to taste. Something like, “We saw the best for more cycles than others, so we are more likely to identify the best now.” Unlike later-stage investing like PE or stock picking, it’s less obvious where the “battle scars” accumulate, or which ones are actually useful. Since VCs have a much lower hit rate than PE (needs to be close to 100%) or stock pickers (should be 52-54%), it’s harder to determine if short- to medium-term success is luck or skill.

Some argue that the best VCs have no false negatives. “Don’t miss the next Google,” is their rough mantra. Others want to reduce the false positives. “Don’t invest in the next Theranos or WeWork.” I actually think both are wrong in that they 1) assume early-stage investors have no influence on outcomes, and 2) are both negative rather than positive filters. But I can’t put my finger on a better mantra. I think it is something like, “Find the next founder of Google, and help him or her succeed to the best of your ability.”

But, as Paul Graham writes:

Path forward: Just be good (?)

Another way to be known as a good investor is to have made universally-acknowledged good investments. “He’s the guy that found Uber.” Unfortunately, this is another lagging indicator. Fortunately, though, it’s a lagging indicator of personal competence.

You don’t get paid when you’re right, you get paid when the market realizes you’re right. Having an opinion and helping the market realize that opinion is correct is a skill. And in startups, frankly, this primarily involves the founder(s) having a good vision and investors helping translate or refine that vision.

Two Analogies

Best I can tell, being a good early-stage investor is like being a good parent. You want your portfolio companies to know the right people, but you don’t want them to be undeserving nepo babies. You want to guide them where they lack experience, but you don’t want to be overbearing. You want to be supportive of them, but you don’t want to be the guy on Facebook shouting every small win from the rooftops. That’s just embarrassing.

Most important to the parenting analogy, being a good investor requires a point of view. That point of view may change (all the eldest children reading know exactly what I mean), but it needs to exist. What you stand for, what future you think can and should exist, and what you have zero tolerance for are all integral to being a good investor. You don’t want an “iPad kid” portfolio company. The “wisdom” investors claim to have is always a little less valuable than investors think and a little more valuable than entrepreneurs think.

I also often say being a good investor is being a good translator. At later stages, this is translating a business to numbers and vice versa. At earlier stages, that is translating a company’s end goal into a business plan, translating legalese into interpretable points of negotiation, and translating opaque risks into “known unknowns.” This helps companies acquire customers, partners, and capital.

My other strongly-held point of view is that, like being a good parent, showing up early and often makes a huge difference. Our companies regularly express surprise that we go to their talks, company events, and board meetings in person. What we lack in podcast presence, we hopefully more than make up for in our physical presence.

Conclusion: Trust the process, but know I’m missing something

I think once you are in the right spot, if your effort is held constant, success is inevitable. I’ve found that most successful people are much less impressive than you’d think in a holistic sense and much more impressive than you’d think in a narrow sense. So it’s very important to trust the process but also constantly question what the end goal of that process is.

I was joking around with one of our portfolio company C-suite execs, who is a killer and relatively young for his role, and he told me (paraphrased), “Dude you’re like a year out of college, I’m excited to see you when you’re 25 and have had your face mashed in a few times.” I responded that I am 25, and that I have had my face mashed in a few times.

He said, “Oh, I thought you were 22.” The unspoken follow up that I read on his face was, “You make a lot more sense now.”

Mice run faster when they are simultaneously chasing the smell of cheese and running away from the smell of a predator. My sense of urgency makes a lot more sense to people when they realize, due to my startup random walk, I started my career meaningfully behind my peers, and I think I can be world class at investing. At my age, I’m officially Silicon Valley old. If I can be as great as I think I can, the clock’s ticking. I’m not playing with house money.

My goal is to become the person about whom your opinion does not change, whether I’m 25 or 35. I have no interest in being precocious. I want to be great.

1  You can listen to me speak (with a lot of ‘umms’ and ‘ya knows’) on a podcast with former NBA Rookie of the Year Michael Carter-Williams (no relation) here. The company is still operating, exclusively on Fanatics’ live streaming platform.